Acknowledgement is made to the MIUR (Rome), FIRB Project (Progettazione, preparazione e valutazione biologica e farmacologica di nuove molecole organiche quali potenziali farmaci innovativi), Università di Bologna, and Fondazione del Monte di Bologna e Ravenna. We also thank Tommaso Quinto for carrying out part of the experimental work.
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Communication
Enantioselective Gold-Catalyzed Allylic Alkylation of Indoles with Alcohols: An Efficient Route to Functionalized Tetrahydrocarbazoles†
Article first published online: 10 NOV 2009
DOI: 10.1002/anie.200904388
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Bandini, M. and Eichholzer, A. (2009), Enantioselective Gold-Catalyzed Allylic Alkylation of Indoles with Alcohols: An Efficient Route to Functionalized Tetrahydrocarbazoles. Angew. Chem. Int. Ed., 48: 9533–9537. doi: 10.1002/anie.200904388
- †
Publication History
- Issue published online: 30 NOV 2009
- Article first published online: 10 NOV 2009
- Manuscript Revised: 10 SEP 2009
- Manuscript Received: 5 AUG 2009
Funded by
- MIUR
Keywords:
- alkylation;
- asymmetric synthesis;
- gold;
- homogeneous catalysis;
- indoles
Breaking the taboo: The direct use of allylic alcohols in catalytic and enantioselective Friedel–Crafts alkylation is described for the first time in the presence of chiral gold complexes. This intramolecular Friedel–Crafts reaction was used to prepare a broad range of functionalized tetrahydrocarbazoles (see scheme; X=Me, F, Br, Cl, OMe; R=Me, Et, tBu; R′=H, Me).